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Enzymatic Production of 15-Hydroxyeicosatetraenoic Acid from Arachidonic Acid by Using Soybean Lipoxygenase

  • Kim, Baek-Joong (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Shin, Kyung-Chul (Department of Bioscience and Biotechnology, Konkuk University) ;
  • Oh, Deok-Kun (Department of Bioscience and Biotechnology, Konkuk University)
  • Received : 2013.10.15
  • Accepted : 2013.11.29
  • Published : 2014.03.28

Abstract

15-Hydroxyeicosatetraenoic acid (HETE), as a mammalian biologically active metabolite, has anticarcinogenic effect. The conditions of producing 15-HETE from arachidonic acid by using soybean lipoxygenase were optimal at pH 8.5 and $20^{\circ}C$ with 9 g/l arachidonic acid, 54.4 U/ml soybean lipoxygenase, and 4% methanol. Under these optimized conditions, the enzyme produced 9.5 g/l 15-HETE after 25 min, with a molar conversion yield of 99% and a productivity of $22.8gl^{-1}h^{-1}$. To the best of our knowledge, this is the first biotechnological production of 15-HETE.

Keywords

References

  1. Brodhun F, Gobel C, Hornung E, Feussner I. 2009. Identification of PpoA from Aspergillus nidulans as a fusion protein of a fatty acid heme dioxygenase/peroxidase and a cytochrome P450. J. Biol. Chem. 284: 11792-11805. https://doi.org/10.1074/jbc.M809152200
  2. Campbell WB, Falck JR. 2007. Arachidonic acid metabolites as endothelium-derived hyperpolarizing factors. Hypertension 49: 590-596. https://doi.org/10.1161/01.HYP.0000255173.50317.fc
  3. Chen GG, Xu H, Lee JFY, Subramaniam M, Leung KL, Wang SH, et al. 2003. 15-Hydroxy-eicosatetraenoic acid arrests growth of colorectal cancer cells via a peroxisome proliferator-activated receptor gamma-dependent pathway. Int. J. Cancer 107: 837-843. https://doi.org/10.1002/ijc.11447
  4. Drouet P, Thomas D, Legoy MD. 1994. Production of 13(S)- hydroperoxy-9(Z),11(E)-octadecadienoic acid using soybean lipoxygenase 1 in a biphasic octane-water system. Tetrahedron Lett. 35: 3923-3926. https://doi.org/10.1016/S0040-4039(00)76703-7
  5. Fauconnier ML, Marlier M. 1996. An efficient procedure for the production of fatty acid hydroperoxides from hydrolyzed flax seed oil and soybean lipoxygenase. Biotechnol. Tech. 10: 839-844. https://doi.org/10.1007/BF00154668
  6. Gibian MJ, Vandenberg P. 1987. Product yield in oxygenation of linoleate by soybean lipoxygenase: the value of the molar extinction coefficient in the spectrophotometric assay. Anal. Biochem. 163: 343-349. https://doi.org/10.1016/0003-2697(87)90234-X
  7. Graff G, Anderson LA, Jaques LW. 1990. Preparation and purification of soybean lipoxygenase-derived unsaturated hydroperoxy and hydroxy fatty acids and determination of molar absorptivities of hydroxy fatty acids. Anal. Biochem. 188: 38-47. https://doi.org/10.1016/0003-2697(90)90525-E
  8. Hiruta O, Nakahara T, Yokochi T, Kamisaka Y, Suzuki O. 1988. Production of 9-hydroperoxy-$\gamma$-linolenic acid by soybean lipoxygenase in a two-phase system. J. Am. Oil Chem. Soc. 65: 1911-1914. https://doi.org/10.1007/BF02546005
  9. Iacazio G, Langrand G, Baratti J, Buono G, Triantaphylides C. 1990. P reparative, enzymic synthesis of linoleic a cid (13S)-hydroperoxide using soybean lipoxygenase-1. J. Org. Chem. 55: 1690-1691. https://doi.org/10.1021/jo00292a056
  10. Jacquot C, Peng S, van der Donk WA. 2008. Kinetic isotope effects in the oxidation of arachidonic acid by soybean lipoxygenase-1. Bioorg. Med. Chem. Lett. 18: 5959-5962. https://doi.org/10.1016/j.bmcl.2008.08.108
  11. Joo YC, Oh DK. 2012. Lipoxygenases: potential starting biocatalysts for the synthesis of signaling compounds. Biotechnol. Adv. 30: 1524-1532. https://doi.org/10.1016/j.biotechadv.2012.04.004
  12. Kermasha S, Dioum N, Bisakowski B. 2001. Biocatalysis of lipoxygenase in selected organic solvent media. J. Mol. Catal. B Enzym. 11: 909-919. https://doi.org/10.1016/S1381-1177(00)00143-0
  13. Moreno JJ. 2009. New aspects of the role of hydroxyeicosatetraenoic acids in cell growth and cancer development. Biochem. Pharmacol. 77: 1-10. https://doi.org/10.1016/j.bcp.2008.07.033
  14. Villaverde JJ, van der Vlist V, Santos SAO, Haarmann T, Langfelder K, Pirttimaa M, et al. 2013. Hydroperoxide production from linoleic acid by heterologous Gaeumannomyces graminis tritici lipoxygenase: optimization and scale-up. Chem. Eng. J. 217: 82-90. https://doi.org/10.1016/j.cej.2012.11.090
  15. Wang Y, Yang Y, Shi M, Li Y, Zhang Y, Zhang Z. 2011. Effect of cucumber extract on soybean lipoxygenase activity and the functional properties of soybean protein concentrate. Int. J. Biol. 4: 111-119.

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